Triethylamine → HCID 131720023, compound

HRID 1781266Notes

Reaction equation

HRID 1781266 reaction equation
[OH:1][CH:2]1[O:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].F[C:12](F)(F)S(O)(=O)=O.C(N([CH2:24][CH3:25])CC)C>C(O)C=C>[CH2:12]([C:2]1([O:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4])[OH:1])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 135191(2R,3S,5R)-oxane-2,3,4,5-tetrol

Product 1

HCID 131720023HCID 131720023, compound

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Conditions

Temperature
0 °C

Procedure

Xylopyranose (15.0 g) was dissolved in allyl alcohol (150 mL) and trifluoromethane sulfonic acid (235 μL) was dropwise added 0° C. The reaction was stirred at 0° C. for 15 minutes and then heated at 80° C. for 4 hours. The reaction solution was then neutralized with triethylamine and evaporated to dryness. Chromatography of the material of silica gel using dichloromethane-methanol (19:1) as eluent provided allyl-xylopyranose (14.9 g).

Workup

  1. customwas dropwise added 0° C
  2. temperatureheated at 80° C. for 4 hours
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-df8ad700d0524d5dbe0290d4c136f968
Source dataset
uspto-grants-1997_05
Patent number
US05633233

Reaction notes

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